1,4-Dioxane → 3-(3-Methylphenoxy)benzoic acid

HRID 1777529Notes

Reaction equation

HRID 1777529 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13]CC)=[O:12])[CH:2]=1.O1CCOCC1>[OH-].[Na+].O>[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([OH:13])=[O:12])[CH:2]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 67974005HCID 67974005, compound

Product 1

HCID 216628243-(3-Methylphenoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 3-(m-tolyloxy)benzoate (0.084 g, 0.326 mmol) in NaOH 1M in water (2 mL) and dioxane (2 mL) was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue washed with dichloromethane, acidified to pH 2 with a 6N solution of hydrochloric acid in water, and extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure to yield quantitatively the title compound which was used without further purifications.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue washed with dichloromethane
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-317ccd35e91e4ce19ed46fbd2d828f49
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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